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Synfacts 2007(2): 0226-0226
DOI: 10.1055/s-2006-955780
DOI: 10.1055/s-2006-955780
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Silica-Supported Scandium/Ionic Liquid Catalyst for C-C Bond Formation in Water
Y. Gu, C. Ogawa, J. Kobayashi, Y. Mori, S. Kobayashi*
The University of Tokyo, Japan
Further Information
Publication History
Publication Date:
23 January 2007 (online)
Significance
An efficient silica-supported scandium/ionic liquid (IL) catalyst system for C-C bond-formation reactions in water was successfully developed. The silica-supported scandium catalysts 1a-e were prepared from a commercially available silica gel in three steps (eq. 1). The Mukaiyama aldol reactions of various aldehydes with silyl enol ethers were carried out in the presence of 1c/[DBIm]SbF6 catalyst in water (eq. 2). Asymmetric aldol reaction of the silyl enol ether 2 with formaldehyde also took place in the presence of 1c/[DBIm]SbF6 catalyst and chiral bipyridine ligand 4 to give hydroxymethylated ketone 3 (eq. 3).